Mattias Sjögren writes on .NET 247 how you can hack the VS .NET debugger to show more useful information about an object in the Watch window.  I must admit, it bugs the life out of me that some objects give you a decent bit of info, whereas others just tell you what they are.

Apparently, you can hack the VS.NET\Common7\Packages\Debugger\mcee_cs.dat file such that you can instruct VS .NET to automatically expand objects.  It can only dig into properties (i.e. no methods).  Googling around, I found http://blog.applicationblocks.com/PermaLink.aspx?guid=72eb29b8-06a4-4b12-a576-f15a3960f10b and http://mark.michaelis.net/weblog/2003/08/20.html.  According to the first one (Shannon Braun), VSTweak (part of PowerTools for Visual Studio .NET 2003) gives you a (rough) IDE to do this.